CAS 442905-33-1 (R)-Xyl-PPhos - Catalysts / Alfa Chemistry

Synonyms

(R)-(+)-2,2',6,6'-Tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine

Molecular Weight

756.85

Molecular Formula

C46H50N2O4P2

Canonical SMILES

COc1cc(P(c2cc(C)cc(C)c2)c3cc(C)cc(C)c3)c(c(OC)n1)-c4c(OC)nc(OC)cc4P(c5cc(C)cc(C)c5)c6cc(C)cc(C)c6

InChI

1S/C46H50N2O4P2/c1-27-13-28(2)18-35(17-27)53(36-19-29(3)14-30(4)20-36)39-25-41(49-9)47-45(51-11)43(39)44-40(26-42(50-10)48-46(44)52-12)54(37-21-31(5)15-32(6)22-37)38-23-33(7)16-34(8)24-38/h13-26H,1-12H3

InChI Key

JRTHAKOHBMETRC-UHFFFAOYSA-N

Melting Point

190-194 °C

Assay

0.97

Optical Activity

[α]20/D +125°, c = 1 in chloroform

Application

(R)-Xyl-PPhos, a white solid, serves an essential role as a ligand in asymmetric hydrogenation processes. It is primarily used for the asymmetric hydrogenation of β-keto esters, 2-arylacrylates, aryl ketones, and various other substrates. By forming complexes with metal precursors such as rhodium (Rh), ruthenium (Ru), and iridium (Ir), (R)-Xyl-PPhos acts as a catalyst in several key reactions. It facilitates the asymmetric hydrogenation of aromatic ketones when paired with ruthenium, the hydrogenation of quinolines with iridium, and the copper-catalyzed asymmetric hydrosilylation of ketones. Additionally, it is instrumental in synthesizing novel chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives through the hydrogenation of substituted quinolines. Furthermore, (R)-Xyl-PPhos plays a critical role in the rhodium-biphosphine-catalyzed asymmetric intermolecular hydroheteroarylation of α-substituted acrylate derivatives.

February 19, 2025

Reliable Catalyst for Asymmetric Reactions

(R)-Xyl-PPhos enhances catalytic efficiency in our lab's hydrogenation processes. Excellent for synthesizing chiral compounds, especially quinolines and ketones. Alfa Chemistry's quality consistently improves our research outcomes.